Shemale Dating Stories

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Orientation
Length
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Infinite Scroll

Buried Treasure

by Dreamswritten on Sep 28, 2020
Romance

It was a beautiful day. The sun was high in the sky but the air was clean, brisk and cool. The crashing of the waves made for a salty air that bathed my nose and lungs. I laid back in my folding chair, enjoying the peace I yearn for even if for a brief couple of hours. I began to drift off when I felt something skate across my feet. I look up then down it...

Sissy Powers Ch. 00 - Prologue

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

Hi! My name is Leo Solo. I used to be a normal guy, just like you. Well, maybe not just like you. I have an 8" cock, for starters. And over the years, I've supplemented that with extensive study of Tantra and other sacred sex, learning how to elevate my lovemaking game to the level of the gods. My fiance, Clara, is very appreciative of my devotion to her ple...

Video Party - An OFS Story Pt. 01

by OffNSFW on Oct 5, 2020
Exhibitionist & Voyeur

Introductory note: The following story features an ongoing character, OFS (Our Favorite Slut), who also appears in "Teamwork: A Gangbang Trilogy," "Tanya Krawczyk," and "One Week." If you enjoy this story, you may enjoy those as well. If you've read them already, thank you for reading this one and for continuing to follow her adventures. - The Author VID...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

Sir Gets Jealous

by Daddysbabygirlxvoid on Jul 20, 2020
BDSM

Oscar sat at his desk just staring at Brad. Oscar was clicking his pen furiously. Brad was talking to Katie, he must have been saying jokes as she never stopped laughing. Oscar's eyes widened when her hand brushed against his. No one knew that Oscar and Katie were dating but he was about to expose them. Brad is the biggest player. Oscar started to scribble d...

Enchanted Alien

by NamelessWanderer on Jul 27, 2020
Sci-Fi & Fantasy

This is a story I made by getting inspired by some actual UFO theories I've seen from those who claimed contact by aliens. Not sure if these stories are true or not -— I guess you could never tell, the only way to know is to see for yourself. Though I did have a lot of fun reading all the mystery around them and the similarities between people's beliefs. Of...

The Coeds: First Week Fuck (Amy)

by SiennaItaly on Aug 31, 2020
Erotic Couplings

NOTE: The Coeds is a series of short stories (some longer than others) about the sexual exploits of six freshman girls at a fictional college. The stories are organized by character, and, occasionally, the same story is told from multiple perspectives. Although it draws inspiration from real-life events (and some of the stories are not too far off), the name...

Maisie and her Manager

by storyteller1999 on Dec 14, 2020
Celebrities & Fan Fiction

It's been four months since I became the manager for the most talented young actress -- Maisie Williams. I am actually a year younger than Maisie. I am 22, in two months, I will be 23 and Maisie will be 24 in four months. Anyway, who cares about age or me. I usually have a pile of work to be done, and loads of scripts and mails, couriers, and I have to mana...

Icy Fingers

by captivate on Oct 6, 2020
Erotic Couplings

Lybee was restless. She didn't know how to tell David that she wanted something, anything, to make their nights more exciting. They had been dating for nearly six months when he suggested moving in with her, to spend their time together and be closer. It took her a week to decide. She thought it over from so many angles, always coming up with the same answer...

Meeting Lindsay Lohan Ch. 01

by rpwilbur on Oct 6, 2020
Celebrities & Fan Fiction

I had been following Lindsay Lohan's career for years. She was wonderful in Parent Trap. She blossomed in Freaky Friday. She grew into a woman during Mean Girls. But I never envisioned actually meeting her, nor what would come from that meeting. Allow Me to introduce Myself. My name is Robert. I am known as Master SweetShadow, a real-life BDSM Master. My sl...